Archangels in the Bible

 Yes. In the Bible, the first recorded appearance of Gabriel is to the prophet Daniel in the Old Testament.

Gabriel appears to Daniel twice:

1. Daniel 8 — Gabriel is commanded to help Daniel understand a vision. Daniel hears a voice say, “Gabriel, make this man understand the vision.”
   
2. Daniel 9 — While Daniel is praying, Gabriel comes again and says he has come to give him “insight and understanding,” including the prophecy of the “seventy weeks.” Centuries later, Gabriel appears in Luke 1:
   

• First to Zechariah to announce the birth of John the Baptist. Gabriel identifies himself by saying, “I am Gabriel. I stand in the presence of God.” - Then to Mary to announce that she will conceive Jesus, the Son of God. So if we're speaking of the order of biblical events, the sequence is:
  

Gabriel → Daniel → Zechariah → Mary. Many Christians find it significant that the same angel who explained messianic prophecies to Daniel is later sent to announce their fulfillment in the births of John the Baptist and Jesus.

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Yes. Among the three named angels in Catholic tradition, Michael, Gabriel, and Raphael, their appearances in Scripture are:

Michael

Michael appears in several books of the Bible:

• Daniel 10:13 — Michael is described as “one of the chief princes” who assists in the spiritual struggle involving the kingdom of Persia. - Daniel 10:21 and 12:1 — Michael is presented as the special protector of God's people, Israel. - Jude 1:9 — Michael disputes with the devil over the body of Moses. (This is Michael's only appearance by name in the New Testament outside Revelation.)
  
• Revelation 12:7–9 — Michael leads the heavenly army in battle against the dragon (Satan) and his angels.
  

Gabriel

Gabriel appears:

• Daniel 8 — interpreting Daniel's vision. - Daniel 9 — explaining the prophecy of the seventy weeks. - Luke 1 — announcing the births of John the Baptist and Jesus.
  

Raphael

You are correct: Raphael appears in the Book of Tobit.

• Throughout Tobit, Raphael accompanies Tobias disguised as a human traveler named Azariah.
  
• At the end, he reveals himself: "I am Raphael, one of the seven angels who stand and enter before the glory of the Lord." (Tobit 12:15)
  

Raphael's mission includes:

• Guiding Tobias on his journey,
  
• Helping deliver Sarah from the demon Asmodeus,
  
• Healing Tobit's blindness.
  

Interesting connection

In Catholic and Orthodox tradition, Raphael's statement in Tobit 12:15 parallels Gabriel's statement to Zechariah in Luke 1:19: "I am Gabriel. I stand in the presence of God." This is one reason the Church groups Michael, Gabriel, and Raphael together as the three archangels named in Scripture.

So the scriptural appearances are roughly:

• Michael — Daniel, Jude, Revelation.
  
• Gabriel — Daniel, Luke.
  
• Raphael — Tobit.
  

And yes, if you're reading the canon in chronological order of events, Gabriel's conversations with Daniel occur centuries before his Annunciation to Mary. his Annunciation to Mary.